Hydrochloric Acid → (3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

HRID 1026643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026643
[CH2:1]([N:8]1[C:16](=O)[C@H:15]2[C@@:10]([CH3:24])([C@@H:11]([CH3:23])[CH2:12][C:13]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.CO.Cl>C1COCC1>[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@@:10]([CH3:24])([C@@H:11]([CH3:23])[CH2:12][C:13]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:14]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 70664804(3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one

Produkt 1

HCID 46909231(3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindoleAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(3aR*,4S*,9bR*)-2-Benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (229 mg, 0.674 mmol) was dissolved in THF (2.6 ml). Borane THF (2 M solution) (6.74 mmol, 6.74 ml) was added and the reaction mixture was heated to 70° C. overnight. MeOH and 5 N aq HCl (4 ml) were then added and the resulting solution was heated at 70° C. for a further 2 hours. The organic solvents were removed in vacuo and the reaction mixture was basified using 4 N NaOH. The aqueous mixture was extracted with DCM (×3) and the combined organic extracts were dried over magnesium sulphate, filtered and concentrated in vacuo to afford a residue that was purified by silica column chromatography (eluting with heptane—heptane: 30% ethyl acetate) to give (3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (52 mg). m/z: 326.3 [M+H]+.

Aufarbeitung

  1. temperaturethe resulting solution was heated at 70° C. for a further 2 hours
  2. customThe organic solvents were removed in vacuo
  3. extractionThe aqueous mixture was extracted with DCM (×3)
  4. dry with materialthe combined organic extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a residue that
  8. customwas purified by silica column chromatography (eluting with heptane—heptane: 30% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3b04be2c8103474ca23e68ae4bfad451
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729274B2

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